Bobson has taught math at New York City public high schools since 2005. He is a three-time recipient of the Math for America Master Teacher Fellowship , a New York State Master Teacher, and a 2014-15 recipient of the New York Educator Voice Fellowship. Bobson has taught courses at all levels of high school math from Algebra 1 to Pre-Calculus, including Math Team, Math Research, and AP Statistics. He is a member of the Advisory Council of the Museum of Mathematics.

Bobson has written and spoken extensively on mathematics education. He was a panelist for the 2012 PBS television program American Graduate: A Conversation with Teachers, hosted by Ray Suarez. In 2013, he co-authored an article about teaching geometry for the National Council of Teachers of Mathematics Mathematics Teacher journal. His op-ed articles have appeared in the Queens Tribune, Washington Post, and Math for America Teacher Voices blog.

Bobson has also worked to improve the quality of education in New York State. In 2015, he served on the New York State Education Department (NYSED)'s Committee for Regents Exam in Geometry (Common Core) Standard Setting. In 2016, he was selected to NYSED’s Common Core Mathematics Standards Review Committee, which reviewed and revised the Common Core standards for the state. As an Educational Specialist for NYSED, he writes and edits questions for New York State high school math Regents exams. He was also a member of the United Federation of Teachers's Common Core Standards Task Force. In 2018, he was selected to NYSED's Evaluation Workgroup to Explore Current New York State Requirements and Best Practices for Teacher and Principal Evaluation.

Bobson graduated from the Bronx High School of Science, Princeton University (B.A., history), the University of Wisconsin-Madison (M.A., history), and St. John's University (M.S.Ed., adolescent education, mathematics), where he received his teacher training in the New York City Teaching Fellows program.

Bobson runs Reach the Source, which contains resources related to Common Core high school math in New York State. His Twitter handle is @bobsonwong.